(Z)-2-(amino(pyridin-2-yl)methylene)-N-methylhydrazinecarbothioamide | 252846-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-2-(amino(pyridin-2-yl)methylene)-N-methylhydrazinecarbothioamide
• 英文别名: 2-pyridineformamide N(4)-methylthiosemicarbazone；1-[(E)-[amino(pyridin-2-yl)methylidene]amino]-3-methylthiourea
• CAS: 252846-47-2
• 化学式: C₈H₁₁N₅S
• 分子量: 209.275
• InChiKey: BIYZVXHFNNODHD-UHFFFAOYSA-N

物化性质

• 沸点：
  319.2±34.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(amino(pyridin-2-yl)methylene)-N-methylhydrazinecarbothioamide 在 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 Zn(N-(3-methyl-4-oxothiazolidin-2-ylidene)picolinohydrazonamide)Cl₂
  参考文献：
  名称：

  Novel Zn(ii)-thiazolone-based solid fluorescent chemosensors: naked-eye detection for acid/base and toluene

  摘要：

  三种锌配合物具有不同配体取代基，显示出由酸/碱蒸汽或甲苯诱导的有趣荧光开关特性。

  DOI：

  10.1039/c6ra06412d
• 作为产物：
  描述：

  2-氰基吡啶 、 4-甲基氨基硫脲 在 sodium methylate 作用下， 反应 4.0h， 生成 (Z)-2-(amino(pyridin-2-yl)methylene)-N-methylhydrazinecarbothioamide
  参考文献：
  名称：

  Novel Zn(ii)-thiazolone-based solid fluorescent chemosensors: naked-eye detection for acid/base and toluene

  摘要：

  三种锌配合物具有不同配体取代基，显示出由酸/碱蒸汽或甲苯诱导的有趣荧光开关特性。

  DOI：

  10.1039/c6ra06412d

文献信息

• Nuclease activity and protein-binding properties of a novel tetranuclear thiosemicarbazide Pt(<scp>ii</scp>) complex
  作者：Jia Shao、Wei-Guo Bao、He Tian、Bing Li、Xiao-Fei Zhao、Xin Qiao、Jing-Yuan Xu

  DOI：10.1039/c3dt52044g

  日期：——

  A novel tetranuclear [Pt4(Am4M)4]·16.25H2O (1), where H2Am4M is the thiosemicarbazone ligand (Z)-2-(amino(pyridin-2-yl)methylene)-N-methylhydrazinecarbothioamide, has been synthesized and characterized by using various physico-chemical techniques. X-ray analysis revealed that the Pt(II) complex consists of a neutral tetranuclear [Pt4(Am4M)4] unit and abundant water molecules. The tetranuclear unit is stabilized by strong intramolecular π–π stacking and thus presents a ship-like eight-membered ring [Pt4S4] with four tridentate ligands peripherally coordinated to four Pt(II) ions, constituting a novel type of “well” structure. DNA and protein binding properties of complex 1 have been studied by UV and fluorescence spectroscopic methods. The binding constant (Kb = 3.05 × 106 M−1) and the apparent binding constant (Kapp = 7.732 × 106 M−1) to calf thymus DNA (CT-DNA) were accurately fitted by two respective non-linear equations, suggesting an efficient DNA intercalative binding mode which was confirmed by viscometric experiments. Furthermore, following agarose gel electrophoresis experiments, we observed that the plasmid DNA pUC19 could be completely digested by complex 1, depending on incubation time and concentration, indicating that complex 1 may possess an effective nuclease activity on DNA. Singlet oxygen (1O2) inhibitors showed an inhibitory effect on the cleavage. Fluorescence spectrometry also detected a medium affinity of complex 1 to bovine serum albumin (BSA) at different temperatures, which was tentatively assigned to a static binding mode. All these results suggested that this poly-Pt(II) complex might exhibit biological action as a potential chemotherapy agent.

  合成并表征了一种新型四核[Pt4(Am4M)4]·16.25H2O (1)，其中H2Am4M是缩氨基硫脲配体(Z)-2-(氨基(吡啶-2-基)亚甲基)-N-甲基肼硫代甲酰胺通过使用各种物理化学技术。 X射线分析表明Pt(II)配合物由中性四核[Pt4(Am4M)4]单元和丰富的水分子组成。四核单元通过强分子内π-π堆积而稳定，从而呈现出船状八元环[Pt4S4]，四个三齿配体与四个Pt(II)离子外围配位，构成一种新型的“井”结构。复合物 1 的 DNA 和蛋白质结合特性已通过紫外和荧光光谱方法进行了研究。小牛胸腺 DNA (CT-DNA) 的结合常数 (Kb = 3.05 × 106 M−1) 和表观结合常数 (Kapp = 7.732 × 106 M−1) 通过两个各自的非线性方程精确拟合，表明通过粘度实验证实了有效的DNA插入结合模式。此外，在琼脂糖凝胶电泳实验中，我们观察到质粒DNA pUC19可以被复合物1完全消化，这取决于孵育时间和浓度，表明复合物1可能对DNA具有有效的核酸酶活性。单线态氧 (1O2) 抑制剂对裂解显示出抑制作用。荧光光谱法还检测到复合物1在不同温度下与牛血清白蛋白（BSA）具有中等亲和力，暂时将其指定为静态结合模式。所有这些结果表明，这种聚 Pt(II) 复合物可能表现出作为潜在化疗药物的生物作用。
• Ruthenium(II) complexes containing 2-pyridineformamide- and 2-benzoylpyridine-derived thiosemicarbazones and PPh3: NMR and electrochemical studies of cis–trans-isomerization
  作者：Angelica E. Graminha、Alzir A. Batista、Isolda C. Mendes、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.saa.2007.07.005

  日期：2008.4

  disfavored by the sterical effect of two bulky groups close to each other whereas the trans isomer is disfavored by the electronic effect of competition of two phosphorous for pi-bonding d orbitals of the metal. Our results suggest that, although both factors may be operating simultaneously, in CH(2)Cl(2) solution the balance of these counterpoising effects favors the formation of the trans isomer.

  获得[RuCl（L）（PPh（3））（2）]与2-苯甲酰基吡啶和2-吡啶甲酰胺衍生的硫代半氨基甲酮（HL）的配合物，并进行了充分表征。该络合物形成顺反异构体。顺式异构体由于彼此靠近的两个大基团的空间效应而受到不利影响，而反式异构体由于两种磷对金属的π键d轨道的竞争电子效应而受到不利影响。我们的结果表明，尽管两个因素可能同时起作用，但在CH（2）Cl（2）解决方案中，这些平衡作用的平衡有利于反式异构体的形成。
• Synthesis, crystal structures, anticancer activities and molecular docking studies of novel thiazolidinone Cu(<scp>ii</scp>) and Fe(<scp>iii</scp>) complexes targeting lysosomes: special emphasis on their binding to DNA/BSA
  作者：Jia Shao、Qiang Zhang、Jing Wei、Zhiguang Yuchi、Peng Cao、Shao-Qing Li、Shan Wang、Jing-Yuan Xu、Shuang Yang、Yi Zhang、Jin-Xia Wei、Jin-Lei Tian

  DOI：10.1039/d1dt02180j

  日期：——

  Novel [CuL2Cl]Cl·H2O (1) and [FeL2Cl2]Cl·MeOH·CHCl3·H2O (2) complexes of (Z)-N′-((E)-3-methyl-4-oxothiazolidin-2-ylidene)picolinohydrazonamide (L) as antitumor agents were designed and synthesized in order to explore DNA and serum albumin interaction. X-ray diffraction revealed that both 1 and 2 were a triclinic crystal system with P space group, which consisted of a positive electric main unit, a

  ( Z ) -N ′-(( E )-的新型[Cu L 2 Cl]Cl·H 2 O ( 1 )和[Fe L 2 Cl 2 ]Cl·MeOH·CHCl 3 ·H 2 O ( 2 )配合物3-甲基-4-氧代噻唑啉-2-亚基)吡啶甲酰肼( L )作为抗肿瘤剂被设计和合成，以探索DNA和血清白蛋白的相互作用。X射线衍射表明1和2都是三斜晶系，P空间群，由一个正电主体、一个负氯离子和一些溶剂分子组成。通过荧光和电子吸收光谱法研究了与 DNA 和牛血清白蛋白 (BSA) 的复合物。结果表明，复合物与DNA之间存在适度的嵌入结合模式，K app值为2.40 × 10 5 M -1 ( 1 )和6.49 × 10 5 M -1 ( 2 )。琼脂糖凝胶电泳实验表明，1和2均表现出明显的DNA切割活性。是一种氧化性 DNA 损伤途径，并且1的切割活性强于2。细胞毒性试验表明1比2具有更有效的抗肿瘤活性。这两种复合物通过高亲和力与
• 2-Pyridinoformamide-derived thiosemicarbazones and their iron(III) complexes: Potential antineoplastic activity
  作者：Angelica E. Graminha、Felipe S. Vilhena、Alzir A. Batista、Sonia R.W. Louro、Roberta L. Ziolli、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.poly.2007.10.008

  日期：2008.2

  The iron(III) complexes [Fe(2Am4DH)(2)]Cl (1), [Fe(2Am4Me)(2)]Cl (2) and [Fe(2Am4Et)(2)]Cl (3) with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me) and N(4)-ethyl (H2Am4Et) derivatives were obtained and characterized by means microanalyses, infrared and EPR spectra. The electrochemical behavior of the complexes was investigated. The thiosemicarbazones and complexes (1) and (2) presented toxicity against Artemia salina at low concentrations. Since this bioassay has a good correlation with cytotoxic activity in human solid tumors, the studied compounds present potential pharmacological applications. (c) 2007 Elsevier Ltd. All rights reserved.
• Vanadium complexes with 2-pyridineformamide thiosemicarbazones: In vitro studies of insulin-like activity
  作者：Isolda C. Mendes、Leida M. Botion、Adaliene V.M. Ferreira、Eduardo E. Castellano、Heloisa Beraldo

  DOI：10.1016/j.ica.2008.04.029

  日期：2009.1

  Reaction of VOCl2 with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me), N(4)-ethyl (H2Am4Et) and N(4)-phenyl (H2Am4Ph) derivatives in ethanol gave as products [VO(H2Am4DH) Cl-2] (1), [VO(H2Am4Me) Cl-2] center dot 1/2HCl (2), [VO(H2Am4Et) Cl-2] center dot HCl (3) and [VO(2Am4Ph) Cl] (4). Upon the dissolution of 1-4 in water, oxidation immediately occurs with the formation of [VO2(2Am4DH)] (5), [VO2(2Am4Me)] (6), [VO2(2Am4Et)] (7) and [VO2(2Am4Ph)] (8). The crystal and molecular structures of 5 and 6 were determined. Complexes 5-8 inhibited glycerol release in a similar way to that observed with insulin but showed a low enhancing effect on glucose uptake by rat adipocytes. (C) 2008 Elsevier B.V. All rights reserved.